Claims
- 1. A compound of formula (I) or a salt thereof: wherein:P1 is pyridyl; P2 is pyridyl; A is a bond or a chain of 1 to 5 atoms optionally substituted by C1-6alkyl; R1 and R2 groups are each independently hydrogen C1-6alkyl optionally substituted by NR12R13, C2-6alkenyl, C2-6alkynyl, cyano, halogen, CF3, NR12R13, CHO, OCF3, COR14, CH2OR14 or OR14 where R12, R13 and R14 are independently hydrogen or C1-6alkyl; n and m are independently 0, 1 or 2; R3 is hydrogen or C1-6alkyl; R4 is a group of formula (i): in which:R6 and R7 are independently hydrogen, C1-6 alkyl optionally substituted by one or more fluorine atoms, C1-6alkylthio, C1-6alkoxy or halogen or a pharmaceutically acceptable salt thereof.
- 2. A compound according to claim 1 in which A is a bond.
- 3. A compound according to claim 1 in which R2 is hydrogen, halogen, methyl, CF3 or OCF3.
- 4. A compound according to claim 1 in which R3 is hydrogen.
- 5. A compound according to claim 1 in which R6 is trifluoromethyl or halogen and R7 is C1-6 alkoxy, C1-6alkylthio or C1-6alkyl.
- 6. A compound according to claim 1 which is:1-[5-(3-Pyridyl)-pyrid-3-ylcarbamoyl]-5-methoxy-6-trifluoromethylindoline, 1-[5-(4-Pyridyl)-pyrid-3-ylcarbamoyl]-5-methoxy-6-trifluoromethylindoline, 1-[5-(4-Methyl-3-pyridyl)-pyrid-3-ylcarbamoyl]-5-methoxy-6-trifluoromethylindoline, 1-[6-(3-Pyridyl)-pyrid-3-ylcarbamoyl]-5-methoxy-6-trifluoromethylindoline, 5-Methylthio-6-trifluoromethyl-1-[6-(pyridin-3-yloxy)pyridin-3-ylcarbamoyl)]indoline, 5-Methoxy-6-trifluoromethyl-1-[6-(pyridin-3-yloxy)pyridin-3-ylcarbamoyl)]indoline, 5-Methoxy-6-trifluoromethyl-1-[6-(pyridin-4-ylmethyloxy)pyridin-3-ylcarbamoyl)]indoline, 5-Methoxy-6-trifluoromethyl-1-[2-(pyridin-3-yloxy)pyridin-4-ylcarbamoyl)]indoline, 5-Methylthio-6-trifluoromethyl-1-[6-(2-methylpyridin-3-yloxy)pyridin-3-ylcarbamoyl)]indoline, 5-Methylthio-6-trifluoromethyl-1-[6-(6-methylpyridin-3-yloxy)pyridin-3-ylcarbamoyl)]indoline, 5-Methoxy-6-trifluoromethyl-1-[6-(pyridin-3-ylthio)pyridin-3-ylcarbamoyl)]indoline, 5-Methoxy-6-trifluoromethyl-1-[6-(2-methylpyridin-3-yloxy)pyridin-3-ylcarbamoyl)]indoline, 5-Methoxy-6-trifluoromethyl-1-[6-(4-methylpyridin-3-yloxy)pyridin-3-ylcarbamoyl)]indoline, and pharmaceutically acceptable salts thereof.
- 7. A pharmaceutical composition which comprises an effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier or excipient.
- 8. A process for the preparation of a compound of formula (I) or a pharmaceutically acceptable salt thereof, which process comprises:(a) the coupling of a compound of formula (II); with a compound of formula (III);D-R4′ (III) wherein A, P1 and P2 are as defined in formula (I), C and D contain the appropriate functional groups(s) necessary to form the moiety —NR3′CO when coupled, the variables R1′, R2′, R3′ and R4′ are R1, R2, R3 and R4 respectively, as defined in formula (I), or groups convertible thereto, and thereafter optionally and as necessary and in any appropriate order, converting any R1′, R2′, R3′ and R4′, when other than R1, R2, R3 and R4 respectively to R1, R2, R3 and R4, interconverting R1, R2, R3 and R4 and forming a pharmaceutically acceptable salt thereof; or(b) the coupling of a compound of formula (IV); with a compound of formula (V); wherein P1, P2, R1′, R2′, R3′ and R4′ are as defined above and E and G contain the appropriate functional group(s) necessary to form the A moiety when coupled and thereafter optionally and as necessary and in any appropriate order, converting any R1′, R2′, R3′ and R4′, when other than R1, R2, R3 and R4 respectively to R1, R2, R3 and R4, interconverting R1, R2, R3 and R4 and forming a pharmaceutically acceptable salt.
- 9. A method of antagonizing 5HT2C receptors by administering to patient in need thereof, an effective amount of a compound of claim 1.
- 10. A method of treating CNS disorders by administering to a patient in need thereof, an effective amount of a compound of claim 1.
- 11. A method of treating anxiety or depression by administering to a patient in need thereof, an effective amount of a compound of claim 1.
Priority Claims (6)
Number |
Date |
Country |
Kind |
9502052 |
Feb 1995 |
GB |
|
9508327 |
Apr 1995 |
GB |
|
9508967 |
May 1995 |
GB |
|
9516845 |
Aug 1995 |
GB |
|
9517542 |
Aug 1995 |
GB |
|
9518574 |
Sep 1995 |
GB |
|
CROSS REFERENCE
This application is a 371 of PCT/EP96/00368 filed Jan. 26, 1996, which is a division of Ser. No. 08/875,506 filed Oct. 16, 1997 U.S. Pat. No. 5,990,133.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP96/00368 |
|
WO |
00 |
7/31/1999 |
7/31/1999 |
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5990133 |
Gaster et al. |
Nov 1999 |
|
Foreign Referenced Citations (3)
Number |
Date |
Country |
WO 9205170 |
Apr 1992 |
WO |
WO 9404533 |
Mar 1994 |
WO |
WO 9422871 |
Oct 1994 |
WO |